The Undertaker is reportedly signed to a 15 year WWE contract.
It was noted in August 2019 that Taker was essentially a WWE lifer due to the "big-money deal" he signed with WWE in the early part of last year. The Wrestling Observer Newsletter now reports that WWE Chairman Vince McMahon signed The Deadman to the 15 year deal after angrily reacting to the non-WWE dates he was booking.
We reported back in August that Taker put ink to the new contract after Vince made him an offer he couldn't refuse financially. There weren't many details on the contract, but it was revealed that the deal includes an agreement that says Taker could no longer work the non-WWE signing dates that he had started to book. This is what led to Taker being pulled from the Starrcast II convention, which ran in conjunction with AEW's Double Or Nothing pay-per-view, in May 2019 after he had already been announced to appear.

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The Observer reported this week that last year when Taker's contract expired, he agreed to do a few appearances, and then broke character to get on social media as Mark Calaway. Vince, after letting Taker go, reportedly got so mad that Taker would actually take non-WWE bookings, that he offered the 15 year deal worth big money.
While not billed as a lifetime contract, the 15 year deal is essentially a lifetime deal as Taker will be almost 70 years old when it expired.
Vince was said to be really upset when Taker's Starrcast appearance was announced last year, but the lucrative contract was offered once things calmed down between the two.
The 15 year deal could be one of the biggest in WWE history, if not the biggest. It was reported in early 2018 that Taker was charging $25,000 per hour for non-WWE signing appearances, and that he would have no trouble getting booked at that price.
Taker hasn't wrestled since the Boneyard Match win over AJ Styles at WrestleMania 36 last month.Source: Wrestling Observer Newsletter

Currently booking tonight’s card...

15 years, Probably intending on taker eventually working behind the scenes in some capacity... probably giving him the freedom to decide when he wants to work his last match and then they’ll make sure he has a spot inside the company after that.

If they do cinematic style matches, and limit his live appearances to a promo or something, then yes.
But I don´t think that´s what he´s really after.. He just saw an opportunity for a guaranteed income for several years. Mark played Vince

Southern Pride

Basically Undertaker is going to be involved in the product in some way for a long time, even if it's occasional appearances or occasional help behind the scenes. Like those Saudi Arabia shows. Even when he isn't on the card he is still involved.

Registered

Basically to give him living money so he doesn't have to do the autograph and trade show circuit. Probably hurts WWE as a brand to have Undertaker doing the flea market circuit even if it's wholly his fault for being stupid with his earnings and hurting for money now.